Profadol
In-game article clicks load inline without leaving the challenge.
Profadol (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis. It acts as a mixed agonist-antagonist of the μ-opioid receptor. The analgetic potency is about the same as of pethidine (meperidine), the antagonistic effect is 1/50 of nalorphine.
Synthesis
The Knoevenagel condensation between 3'-Methoxybutyrophenone [21550-06-1] and Ethyl cyanoacetate gives (1). Conjugate addition of cyanide gives (2). Hydrolysis of both nitrile groups, saponification of the ester and decarboxylation gives the diacid, (3). Imide formation occurs upon treatment with methylamine giving 3-(3-Methoxyphenyl)-1-methyl-3-propylpyrrolidine-2,5-dione, (4). Reduction of the imide by lithium aluminium hydride gave [1505-32-4][29369-01-5] (5). Demethylation completed the synthesis of Profadol (6).